The Right Timing
by forgetablelove
Summary: (television series universe) With Jenny back in the city, can Nate reconnect with her (Set just after the 5 years later fast forward at the end of the series.)


i[Set in 2017 (five years after Gossip Girl is revealed, the same time as the 5 years fast forward in the last episode of the series)]/i

It was snowing. The fluffy, white flakes fell to the ground and stuck, making the sidewalk slick as Nate Archibald walked along. He was headed for a breakfast with Chuck. Blair was busy with work this morning and Henry was off in some lesson. They truly did try to give Henry the world, which Nate admired. Chuck was definitely set on not being his father and not letting Henry become who he had been during school. In the end, Chuck had gotten everything he wanted and more out of life, but he seemed more than aware of his faults in his youth that he didn't want his son to repeat. Nate was impressed with his friend for that insight. Who knew Chuck Bass would ever become insightful? For all the years he had a part of Chuck and Blair's life, he had rarely seen Chuck go to back into the actual black in his soul. It was odd that it seemed that Chuck and Blair had gotten what they had always wanted in the most desperate circumstances, but were thriving with the outcome and in the aftermath anyway. Dan and Serena had gotten what they had wanted too despite all the drama that had follow them around since the beginning. Recently, Dan and Serena had gotten married in a private and intimate ceremony that they wanted the press and eyes from the outside out of. It was about them, like Chuck and Blair's wedding years ago had been about them as well. It was something that had changed after high school with all this friends. Rather than being the ones that society tried to focus on and reveling in the attention, they just decided they would rather be seen for their professional achievements rather than their personal lives. It seemed to make all of them happy and they thrived. All of them, including himself, seemed to thrive after Bart Bass was finally dead and they all seemed to grow up almost instantaneously.

It had been years, but he knew they all still thought of Bart Bass's death. They had to. Lily had remarried her first husband, William, and Rufus was finding happiness with another member of the music industry. Georgina and Jack had actually surprised them all. They had found love and family - with each other. Jack was a surprisingly good and interesting stepfather to Georgina's son, Milo. He may not win stepfather of the year, but he still impressed them all. Who knew that Jack Bass had a heart? Perhaps somewhere deep down, Bart had knew that he was the only one that was truly heartless in the Bass family and for years he'd had just tried to keep all the Bass men who could overthrow him down. Nate didn't believe that Bart had deserved to die - since no one did - but he couldn't say that any of them were feeling a true loss at the man's death. It was almost like a weight had been lifted off of Chuck, Jack, Blair, Lily, and Rufus as well as the others by association. They were finally able to breathe without the pressure of what Bart Bass might do if they stepped out of line in his eyes.

The Spectator was going well. After all the controversy and hard times in the past, it was over. It was one of the leading online magazines with companies practically lined up to advertise on the internet magazine's website. Now, the city politics was catching up with him again. His grandfather was still trying to get an Archibald or Van Der Bilt in public office. With Trip having gone off the deep end, his grandfather still seemed to think that Nate was the next best family candidate. He disagreed. He knew better and knew how to work the political field enough to not publicly announce his refusal to run for mayor or any other public office in the city, but he had no intention of ever doing so. Politics had ruined his cousin and grandfather and he refused to allow the same thing to ruin him. He was content with running the successful Spectator. He was content with being his own man for one of the first times in his life. It was something that five years ago Chuck and he decided between themselves. They were done allowing their families to dictate who they were. They decided instead.

As he ducked into a coffee shop, he went straight to the counter and ordered a coffee with a smile. Stepping back from the counter a little to allow someone else to order, he was surprised when a blond woman turned. Jenny Humphrey smiled immediately when she saw Nate standing there. Less than a year ago, Jenny had returned to New York City with the ban on her presence had been lifted finally. Blair had even given Jenny her own fashion line within her company Waldrof Designs called "J for Waldrof" which was a success. It seemed that most of their past grievances from high school and even college had just became obsolete as they all took control of their lives rather than letting someone else do it for them. He smiled in return at the sight of Jenny.

"Nate! I didn't expect to see you!" she said, happily as she managed to throw her arms around him and give him a hug without burning him with the cup of coffee that she held in her hand. He wrapped his arms around her as well, giving her a friendly hug in return.

When they both moved back to break the embrace, he continued to smile and answered, "Coffee before heading into the office," he said, gesturing toward the counter where he still waited for his order.

She held up her coffee. "Me too. I have to go into the office and work on some new pieces for the line. I think Blair might try to fire me if I don't have at least two good pieces before the end of the day," she said with a grin. It was clear that most of Jenny and Blair's turbulent relationship had calmed down since Jenny's return, but Nate actually thought there was probably a thread of truth to her words. Blair was a hard woman to please. He had dated her long enough to know that well and has always been her friend after even their few breakups. She drove those who worked for her hard, expecting only the best, including from Jenny. Perhaps actually more from Jenny with her past with the girl.

Despite all they have overcome, they were all still the people they had been in high school deep down below their new surfaces as adults since the core of who they were never changed at the core.

He nodded, glancing around him. "Did you have a moment to sit there then? We can drink our coffee and then trek back into the office for another day after?" he offered, gesturing toward an empty table nearby.

She seemed to weigh the pros and cons of having coffee with him and possibly being late for work in her head for a second before she nodded. It wasn't real hesitance. He knew how Blair could be and actually smiled. At least she took her job seriously, that was more than some might given the circumstances. Being the head designer on a whole line, some might say that she should reap the benefits and not worry about being late or something trivial as that. Without missing another beat, she moved to the table he'd pointed out and sat down, pointing behind him at the counter. "I think your order is up," she said.

He turned around and saw that the girl behind the counter was trying to get his attention to give him his coffee. It was a simple order and suddenly, with the agreement of Jenny to sit and talk for a bit, he wished he'd bought more than just a coffee, actually. He nodded his polite thanks and took the coffee to go sit across from Jenny. "So, other than Blair expecting the best as always, how are things? We really haven't had a chance to check up since you moved back."

"We've both been busy," she said easily, sipping at her coffee. "I read something of you running for mayor? I'd vote for you." She looked at him with a quiet inquiry, something that she seemed to have had to mature into. She used to be as direct and wanting that gossip, that news, those answers as anyone else, but now she seemed to have this quiet maturity about her. In a way, this could just be another game.

He didn't hesitate to just shake his head. "Between you and I, no, I'm not. My grandfather wants me to, but I'm not. I just know better than to just flat out announce that I'm not going to."

"For your grandfather's sake or yours?" she asked, for a split second turning back to the same girl she may have been before she was shipped off to Hudson and then to college in London.

"Both. I don't want the Spectator to be affected," he said with a shrug, taking sip of his coffee in a nonchalant way.

"For your grandfather then," she said without shame. He was almost impressed by her bluntness and the fact she seemed to be dying to read between the lines, to search for the truth behind the words.

"I don't want to upset or disappoint him. After what happened to Trip, I think it would be better if I just play my cards right and let him think as he wishes. I don't have to do anything I don't want to, but why do I have to announce it?" he asked, casually.

"You're right..." she said slowly, like she was thinking of what she said carefully. She paused, staring at him for a moment. "But isn't it just deceiving everyone to tell everyone by not telling them?"

"No. I'm not lying. I didn't tell them anything either way," he said with a shrug. "In the end, there are no shortages of prospects and people to run. They don't need me. I like being the owner of the Spectator. I like being known for that."

"You worked hard to get where you are," she agreed.

"Well, that's debatable, actually. Did any of us actually work hard? I mean, maybe you did more so than the rest of us, but we were handed a lot by our friends and family. Even Blair of all people gave you a fashion line," he pointed out, shamelessly.

She grinned at him, surprising him by the reaction. "We all know the paper would failed if you weren't good at your job and deserve it. And Blair never would have given me a job if I didn't deserve it and work to maintain it. Blair would fire me if I fail and we all know it," she said with confidence and conviction.

"Still from Brooklyn, I see," he said teasingly. But she had a point. She had a point more than she knew. Even if they didn't work for what they got, they worked to maintain it. They held onto what they had with a tight grip to try not to lose it. Being from Brooklyn, it seemed like Jenny almost always had to work for what she had. She graduated high school with the shadow of Gossip Girl being behind her while she graduated college on her own accord with hard work and never giving up.

"I live in Brooklyn again," she said proudly.

He blinked, surprised. Did she live in Brooklyn? Clearly, they weren't as close as they once were. They had never been close after the guerilla fashion show. He wasn't even sure where she lived now. She seemed to have easily forged her own path when she came back without the group. Dan and Serena had moved on. Blair and Chuck were married with Henry. He was... well, what was he? And what happened to Vanessa? She seemed to have disappeared, never to return. Surely, she spoke to Dan still, right? But she wasn't even at the wedding. The ceremony had only included those close. Come to think of it Jenny had avoided him. It was an abrupt realization. She had been avoiding him and here he was, practically forcing his presence on her. "I'm surprised you don't live in the Upper East side with the rest of..."

"The rest of us?" she supplied for him when he trailed off.

"Well, yeah," he said, more than a little unsure of himself.

"My dad is back in Brooklyn, too. It seems Dan is the only one who isn't," she said with a shrug.

Dan lived with Serena in a place on the Upper East Side, about five minutes from Blair and Chuck. No one lived in the hotel anymore. No one wanted to. Chuck ran it, but no one lived there as they once had. They had all moved on. Jenny had, apparently, just moved back to where she was comfortable. It made sense, but it wasn't something that had occurred to him before. "I didn't realize that Rufus was back in Brooklyn."

"Same loft. I'm sure you remember your stay there," she said with a grin.

"I do," he said, not quite relaxing at the memory.

As if sensing his unease, she smiled and nodded. Slowly, she drained a bit of her coffee and stood up. "I should get to work. Blair might already be on the warpath," she said as if it was nothing.

Nate just nodded. "Yeah. Yeah. See you," he said in a nonchalant way. As she got up and left the coffee shop with a wave, he couldn't help but wonder how uncomfortable, uneasy, and strange it had been between them. "Good luck." he said more to himself than the young woman who disappeared through the door.

Nate sat behind his desk as he read through and examined the papers before him. There was a lot of behind the scenes things to do with the paper, but most of it was boring. Most of it was just normal, mundane paperwork that he had to look over and oversee. He had to give his permission on so many things that sometimes it drove him crazy. It was the same thing every day. Glancing at the clock, he noticed it was just after noon. The idea of lunch jumped out at him immediately at the time. He set aside the work he was looking at and grabbed this things, trying to slide of the office before someone came into the office with another problem.

Even living on the Upper East Side his whole life, he had never really cared about fashion. With his lack of interest, he had never ventured into Waldrof Designs, but on his lunch break, he found himself heading there without noticing or planning. He nodded his way into the building and into the design studio, not remembering a time that he'd been in one. He noticed Blair at first - running around the studio and barking demands at people. Apparently, she didn't like the blue in a dress. She wanted it available and shown in a mauve instead. What color was mauve? It sounded depressing, actually, as a name of a color.

Coming out of a doorway without looking, Jenny ran right into Nate. Startled, she stepped away as they bounced off each other nearly. His hands went out in reflex to catch himself on the nearest surface - a desk - at the unexpected collision. He grinned, letting out a small laugh as she gasped and blinked. "We meet again," he said, still with laughter in his voice.

She grinned. "I guess we do! What are you doing here?" she asked, barging forward into the conversation without missing a beat. She was carrying a folder and before he could answer, he already head Blair calling for her in that demanding tone that only Blair processed that used to strike fear into the girls at Constance Billiards school and some of the boys at St. Jude's too. Jenny peered over Nate's shoulder, eying Blair and seeming to access what she should get away with. Clearly deciding that she couldn't get away with just ignoring Blair, she gave Nate a nearly apologetic smile and said, "Sorry. I gotta go."

Nate reached out his hand and stopped her just as she started to slide around him to go to Blair. "Wait, Jenny. Jenny-" He paused, feeling unsure of himself. Was he really going to ask this? What if the answer wasn't what he wanted to hear? "-Jenny, are you avoiding me?"

There. It was out there. It was between them. She could answer how she wanted to or at least that's what he told himself.

She froze, looking back at him with a confused and surprised expression for a moment. "What? No! I mean, no! Why would I be avoiding you?" The puzzlement was obvious in her tone, like the thought had never even occurred to her before now. Immediately, he felt like a fool for thinking that or asking.

"You haven't been around... since you moved back," he said, weakly, a little taken back by her own reaction to his question.

She frowned - a small nearly graceful expression forming on her familiar face. She'd grown up since Constance Billards, but she was still Jenny. He knew her and she hadn't changed that much. "I've been busy," she said. At Blair's new call, a little more persistent if that was possible, she let out an exasperated sigh. "I... I gotta go. Call me, okay? I'm not avoiding you. Call me," she said, repeating herself firmly.

He nodded just as she turned away, heading to Blair. If he didn't know better he could have sworn that she had rolled her eyes at Blair's demands and the idea she might have actually made him grin. He liked the idea that nothing really had changed. Blair immediately started to drill her with requests, questions, and her opinions as Nate stood back for a moment and watched how the pair interacted. Seeing them actually react to each other in a near professional way was a bit surprising as well as interest. He wasn't accustomed to seeing this. Serena and Blair used to declare war on each other all the time and make up in the end, but who would have thought that Blair and Jenny would have gotten over things? They had had a war that more than riled any of Serena's and Blair's and it had went for years so far as banning Jenny from Manhattan.

Since both of them were enthralled in the work before them, he merely gave a small attempt at an awkward wave before he left again. He only remember after that he wasn't sure he had the correct number for Jenny which made him pause as he headed into the office again.

Digging out his cell phone later that night as he laid on his bed, he scrolled through the numbers and landed on Jenny. He still wasn't sure it was still the correct number, but he couldn't help but try to call. It rang twice, making him think that he didn't have the correct number after all before he heard the ringing stop abruptly with a short pause of silence before the familiar voice came over the line. "Hello?"

"Hey, Jenny?" he asked into the phone. Suddenly, he was unsure despite the fact he knew he had the right number now.

"Nate!" Jenny's voice now sounded excited and happy. "Hey. What's up?"

He paused, shifting on the bed to put the arm that wasn't helping holding the phone to his ear behind his head as he relaxed. It seemed almost like effort to relax right now, but he was trying to. "Nothing. I just... You said to call," he reminded her.

"Yeah. And you did."

"You sound surprised."

"I've been back for months. We went to the wedding..."

"So?"

"Well, you could have been avoiding me."

He chuckled, suddenly relaxing as he rolled his eyes toward the ceiling. "I wasn't avoiding you."

"Well, I know that now."

"Yeah you do."

"And you know I wasn't avoiding you."

"Yeah, I do, too."

There was a silent, uncomfortable pause before she asked abruptly, "So why haven't we hung out? You'd think would have."

"I don't know. We've been busy, like you said."

"That's an easy answer, Nate. What's the real answer?"

"Do you want to hang out?"

Again, the pause. He had no idea what to make of the pauses. For a moment it seemed easy and nature and then suddenly there was a pause on the other end of the line and he had no idea. If she didn't want to talk to him then why did she answer? His number hadn't changed. He was sure if she didn't just delete him from her phone book his name would have popped up with his call. "Yeah." A simple answer. One word.

He sat up on the bed, cradling the phone to his ear. "What are you doing now?"

"Now?"

"Now. What are you doing now?" he asked, trying not to sound persistent.

"Nothing. I just got home."

"Blair works you that hard?"

"It's the fashion world. It never sleeps," she said simply, seemingly uninterested in that part of the conversation.

"Do you?"

"Of course I do."

"So, are you planning to sleep now?"

"What? No. I... What?" she asked, clearly confused.

He had no idea where he was going with that line of conversation, but it really didn't matter to him. He chuckled at the reaction, actually. "Well, if you're home, you're not doing anything, and you're not going to bed, why can't we hang out now?"

There was a soft "ah" from the other side of the phone and then a tone that he was sure she was smiling as she spoke. "When you put it that way, I don't see why not," she said with a soft laugh too behind her words.

"Meet you at the Empire in ten minutes?" he asked, already starting to get up off the bed. He was strangely excited to go.

"Okay," she said, "See you in ten." Then the line went dead in a blank silence back at him which just made him laugh at her apparent own excitement and the fact she didn't hide it at all. He got up, put his cell phone in his pocket, and just left. It probably wouldn't take him the entire ten minutes to get there since he lived close by, but he wasn't going to just wait around. He was sure that it would take her longer than ten minutes to get from her exclusive place in Brooklyn to the Empire. It normally took longer coming from the other boroughs, not that it had been much of a problem for her before.

He waited in the bar of the Empire for nearly twenty minutes before she strode in. It would have been impossible not to see her as she walked in with her head held high and her pale blond hair flowing down her back. Strangely, Jenny had grown up almost before his eyes. Yet, he didn't quite remember it happening. One day she was the golden blond who was trying to be in the in crowd with Blair and sitting below Blair on the Met steps and the next it seems she was the girl who spoke her mind and took the crown at Constance Billards for herself like it was always hers. Now she was a professional designer with her own line and clothes she designed in stores who held herself like with confidence and indignity. The crown there had always belonged to her, she just forgot for a bit how she had been and had to be reminded. After the reminder, she was back to the same Jenny. She didn't hesitate to walk right up to where he sat and sit there beside him with a smile on her face.

"Hey," he greeted her.

"Hey," she returned, looking at him as if she expected something. What did she expect? Did she want anything from this, from him? "We're not sleeping."

He looked around and then at her again with a grin. "No, we're not. Are we supposed to be?"

"Well, it's what? Midnight? Aren't we supposed to be responsible professionals who sleep?"

"Before work?"

"Well, at night..."

"No, we aren't. Why would we be? As long as we get to work, we can sleep at our desk," he said, still grinning.

"Sleep at my desk? I think Blair would do something mean to me if I did that!" she exclaimed with a laugh.

"Are you still afraid of Queen B?" he asked teasingly.

"I was never afr-"

He cut her off with a pointed look and tilt of his head.

"Okay. I was a little scared back in the beginning, but I haven't been for years! And Blair has changed... sort of."

He smirked. "Sort of?"

"She's always going to be Blair," Jenny stated in a matter of fact tone.

He conceded to her point with a nod. "Yeah, she is. But is that so bad? Is Blair so bad?" he asked, knowing that Blair had her faults but Blair was his friend. She'd been a lot of things in his life, actually, but she was still his friend. There was no reason to deny who she was or how she was. They both knew the truth and even Blair knew the truth. But yes, Blair had changed sort of in her own way. They had all grown up.

Jenny shook her head. "No. She's not when she's not declaring war on you. She's almost... decent when she's not being the mean girl," she said with a shrug.

He smiled a little. "She is decent. She's more than decent."

She returned the small gesture of a smile and nodded. It was clear she suddenly didn't want to talk about this. Some wounds couldn't be healed and he was sure, looking at her now, that some of the wounds that Blair had left on her during their war and she had left on herself by trying to keep up hadn't just healed. They had turned to scars. They were permanent. It was almost sad to realize. He wanted more for Jenny, but he really couldn't do much about it, actually. Clearing his throat, he decided to try to change the topic. "How do you like working? Or even being back in the city?"

She smiled again, this time bigger and more genuine. "I love being back in the city. And I love my job. I get to do what I always wanted. I design clothes that I'd want to wear. It's still a thrill to see other people in my designs. It's still exciting to go to the store and see my designs being sold. I don't think I'll ever get used to it," she gushed for a moment with great pride and enthusiasm.

He grinned back. "You deserve it."

"Thank you, Nate. I know we didn't... exactly... you know... It wasn't easy," she said, suddenly stumbling over her words and seeming to make no sense.

He raised his eyebrows at her, confused for a moment. "What wasn't easy?"

"What happened," she said softly. "How it all happened. I liked you a lot, but you were always with someone else."

"Oh," he said softly, catching on. He could remember the moments they had shared, the moments that they'd been there for each other, and even how they had never caught quite up. Something was always in their way whether it was Dan or the fact she was driven out of Manhattan when she had slept with Chuck. "It was never the right timing."

She looked down for a moment and then back up at him, a curious and hopeful expression on her face. "Is it the right timing now?"

"Now?" he echoed and then he grinned. "Now seems like the perfect time."

"So, what? We finally got it right?" she asked, a grin spreading across her face.

He nodded, shifting so he moved closer to her. "We finally got the timing right," he said softly as he leaned forward. Reaching up, he gently tilted her face toward his, holding her chin lightly in his hand as he leaned forward to kiss her. She leaned toward him as well, welcoming the kiss though there was a hint behind more than movements that held a certain shyness. Neither wanted to be burned again. Neither wanted to be wrong. They wanted this to be right. The moment her lips touched his, he was sure the timing was right.


End file.
